Chemical constituents of Patrina scabiosaefolia / 中草药

Objective: To study the chemical constituents of the herbs of Patrina scabiosaefolia. Methods: Many column chromatographies such as silica gel, Sephadex LH-20, ODS column chromatography and preparative high-performance liquid chromatography were used to separate and purify the chemical constituents of P. scabiosaefolia. The structures of these compounds were identified by physical-chemical data and spectroscopic techniques. Results: Eighteen compounds were isolated and purified from the ethanol extract of P. scabiosaefolia, and their structures were identified as follows: 6-methoxy-7-(1’-henicosacyloxy- 3’-hydroxy-2’-propoxy) coumarin (1), oleanolic acid (2), ursolic acid (3), palmitic acid (4), dodecanoic acid (5), α-tocopherolquinone (6), maslinic acid (7), 4-hydroxy-3-methoxybenzaldehyde (8), 2,6-dimethoxy benzoquinone (9), 3β-acetyloxy-12-en-28-ursolic acid (10), α-tocospiro B (11), 22E-3β-hydroxy-5α,6α-epoxyergosta-22-en-7-one (12), 2α-hydroxy ursolic acid (13), linoleic acid (14), β- sitosterol palmitate (15), 3-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-1-propanone (16), burselignan (17), and hederagenin (18). Conclusion: Compound 1 is a new compound named scabiosaelactone and compounds 6, 8, 9, 11, 12, 16, and 17 are isolated from the genus Patrina for the first time.

Effects of benzoquinone of Averrhoa carambola L. Root on glucose and lipid metabolism, oxidative stress and inflammatory injury in diabetic mice / 中国药理学通报

Aim To investigate the therapeutic effects of benzoquinone of Averrhoa carambola L. root (BACR) on streptozotocin (STZ)-induced diabetic mice and its mechanism. Methods The diabetic model was induced by intravenous injection of STZ in mice. Drugs were intragastrically administered to mice for 21 days. Fasting blood glucose (FBG) and the change of body weight were measured every 7 days. The levels of the total cholesterol (TC) , triglyceride (TG) and low-density lIPoprotein cholesterol (LDL-C), high-density lIPoprotein cholesterol (HDL-C), monocyte chemoattractant protein-1 (MCP-1) , inter-leukin-IP(IL-lp) in serum and uperoxide dismutase (SOD) , malondialdehyde (MDA), glutathione peroxidase (GSH-Px) in liver tissues were measured after administration. The pathological changes of liver tissues were observed by HE staining. The expression of Tolllike receptor 4 (TLR4), myeloid differentiation factor 88 (MyD88) , nuclear factor-kappa B (NF-kB) were observed by immunohistochemistry. Result Compared with model group, the levels of TC, TG, LDL-C, MCP-1, IL-1 p in serum as well as MDA in liver markedly decreased in BACR groups while HDL-C lev-el, the activities of SOD and GSH-Px increased. HE staining showed that BACR improved the pathological condition of liver tissues. The protein expression of TLR4, MyD88, NF-kB were obviously up-regulated. Conclusions BACR could reduce blood glucose, blood lIPid on diabetes mellitus, and its mechanism may be related to inhibiting the release of inflammatory factors and enhancing antioxidant capacity.

Effect of reactive oxygen species on 1,4-benzoquinone-induced mitophagy / 预防医学

Objective To investigate whether the metabolite of benzene, 1, 4-benzoquinone (1, 4-BQ) , can activate PINK1/Parkin-mediated mitocphagy and the role of reactive oxygen species (ROS) in 1, 4-BQ induced mitophagy in vitro. Methods Human promyelocytic leukemia cells HL60 were used as the test cells, and were divided into control group, 1, 4-BQ group (10 μM 1, 4-BQ treated cells for 24 h), NAC group (5 mM antioxidant N-acetyl cysteine treated cells for 24 h) and 1, 4-BQ+NAC group (5 mM NAC preincubated for 1 h prior to the treatment with 10 μM 1, 4-BQ for 24 h) . The ultra structure of the cells were observed by transmission electron microscopy (TEM), and the expression of mitophagy related protein LC3, PINK1 and Parkin were detected by Western blot, and the intracellular ROS content was determined by DCFH-DA staining. Results The mitochondria in the control group showed a normal rod-shaped structure with clear mitochondrial cristae, while in the 1, 4-BQ group, the mitochondria showed a swollen structure with less mitochondrial cristae, and typical double-membrane mitophagosomes were observed. LC3-Ⅱ/LC3-Ⅰ ratio, the expression of PINK1, Parkin protein and ROS content in 1, 4-BQ group were increased compared with the control group (P <0.05) , and this increase was markedly blocked by the co-treatment of 1, 4-BQ and NAC (P <0.05) . Conclusion The 1, 4-BQ can induce PINK1/Parkin-mediated mitophagy and ROS plays a significant role in 1, 4-BQ-induced mitophagy.

Limits of occupational benzoquinone exposure in workplace air / 中国职业医学

OBJECTIVE: To formulate a limit of occupational benzoquinone in the air of workplace. METHODS: According to GBZ/T 210. 1-2008 Guide for Establishing Occupational Health Standards--Part 1: Occupational Exposure Limits for Airborne Chemicals in the Workplace,the relevant literatures on toxicology,epidemiology and foreign occupational exposure limit for benzoquinone were collected and analyzed. A benzoquinone production enterprise was selected as the research subject. Occupational hygiene investigation and occupational epidemiological investigation were carried out. The occupational exposure limit of benzoquinone in the air of workplace was assessed. RESULTS: The literature data analysis results showed that benzoquinone is a highly toxic substance,has strong stimulated effect on human respiratory tract,eyes and skin. The occupational exposure limit of benzoquinone in the workplace air in the United States of America,Germany and Australian is 0. 400 mg/m~3. In the benzoquinone production enterprise,the median of concentration-time weighted average of benzoquinone exposed workers( exposure group) was 0. 100 mg/m~3. The median of concentration-short term exposure limit in the workplace air was 0. 160 mg/m~3. There was no significant difference on the abnormal detection rate of conjunctivitis,dermatitis,and abnormal liver B type and abnormal kidney B type ultrasound between the exposure group and the control group( P > 0. 05). There was no significant difference on the serum liver function and renal function indexes between the two groups( P > 0. 05). The results of blood routine examination in the two groups were within the normal reference range. CONCLUSION: It is suggested that the permissible concentration-time weighted average of benzoquinone in the workplace air should be set at 0. 400 mg/m~3 in China.

Chemical constituents from pods of Glycine max / 中草药

Objective: To investigate the chemical constituents from the pods of Glycine max. Methods: The chemical constituents were isolated by repeated silica gel chromatography, Sephadex LH-20 gel column chromatography, medium pressure column chromatography, and semi-preparative liquid chromatography. Their structures were elucidated by chemical properties and spectroscopic analyses. Results: Fourteen compounds were identified to be 4,4'-diphenylmethane-bis (ethyl) carbamates (1), 2,6-dimethoxy-1,4-benzoquinone (2), (+)-medioresinol (3), taraxerone (4), lupenone (5), 7,3',4'-trihydroxyflavone (6), coumestrol (7), indole-3-carboxylic acid (8), apigenin (9), phaseol (10), 7,4'-dihydroxyflavone (11), stigmasterol (12), β-sitosterol (13), and β-daucosterol (14). Conclusion: Compounds 1-5 are obtained from the pods of G. max for the first time, and compound 6 is obtained from this plant for the first time.

Chemical constituents in roots of Ilex kudingcha / 中草药

Objective: To investigate the chemical constituents in the roots of Ilex kudingcha. Methods: Column chromatography such as silica gel, Sephadex LH-20, and preparative HPLC were used to isolate and purify the compounds. Spectroscopic methods like MS, 1H-NMR, and 13C-NMR, and physical constants were used to elucidate their structures. Results: Nineteen compounds were isolated from 95% ethanol extracts of I. kudingcha, including α-aromadendrol-3β-palmitate (1), β-sitosterol (2), α-amyrin (3), 3-acetoxyolean-12-en-28-ol (4), 3-acetoxyurs-12-en-28-ol (5), 3β-acetoxyurs-12-en-28-al (6), oleanolic acid (7), ursolic acid (8), quercetin (9), daucosterol (10), ficuscarpanoside B (11), 3β-hydroxy-28-norurs-12, 17-dien (12), siaresinolic acid (13), pomolic acid (14), α-D-glucose (15), 2, 6-dimethoxy-benzoquinone (16), syringaldehyde (17), dibutyl phthalate (18), and ilexoside D (19). Conclusion: Compounds 6, 12, 16-18 are isolated from the plant for the first time. Compound 11 is isolated from Ilex L. for the first time.

Cloning and expression analysis of MPBQ MT gene in safflower / 中草药

Objective: Safflower (Carthamus tinctorius) is an important natural source of vitamin E. 2-Methy-6-phytyl-1,4- benzoquinone methyltransferase (MPBQ MT) is a key enzyme in vitamin E synthesis pathway. MPBQ MT gene was cloned, bioinformatics was analyzed, and expression was analyzed to provide the foundation for the biosysthesis and regulation mechanism of vitamin E in safflower. Methods: According to the intermediate sequence obtained from the database of the safflower seed,MPBQ MT gene sequence was cloned by RT-PCR and RACE techniques, and the protein characteristics were analyzed using bioinformatics and constructing phylogenetic tree. The expression of MPBQ MT gene in the different development stages was analyzed using real time-PCR. Results: The full cDNA sequence of MPBQ MT gene was 1 392 bp, named CtMPBQ MT, contained an open reading frame (ORF, 1 038 bp), and encoded a protein of 345 amino acids with a predicted molecular mass of 38 900. The conserved structural domain analysis showed that it had the typical functional domains of SAM protein. Sequence alignment and phylogenetic tree analyses showed that the MT MPBQ gene had some homology with other amino acids, and among them CtMPBQ MT had 89% and 86% of consistency with MPBQ MT of Helianthus annuus and Lactuca sativa. The expression of CtMPBQ MT gene in safflower seeds at different development stages was determined by quantitative real-time PCR, it was found that the highest expression level of CtMPBQ MT gene was detected in 50 d after flowering. Conclusion: MPBQ MT gene of safflower is successfully cloned, analyzed, and expressed, meantime a basis for the study on matter in the synthesis and regulation of vitamin E is provided.

Quantitative HPLC Analysis and Extraction of 2,6-dimethoxy-1,4-benzoquinone from Ficus foveolata Stems

An antibacterial benzoquinone, 2,6-dimethoxy-1,4-benzoquinone, isolated from Ficus foveolata stems was used as a standard marker for establishment of quantitative HPLC analysis for the stem extracts of F. foveolata . The method utilized a TSK-gel ODS-80Ts column (5 microm, 4.6 x 250 mm) with the mixture of methanol and 5% acetic acid in water (24:76, v/v) as the mobile phase at a flow rate of 1 mL/min, and quantitative detection at 289 nm. The parameters i.e. linearity, intraday and interday precision, accuracy, specificity and sensitivity of the method were evaluated for method validation. The recoveries of the method were 99.5 - 103.6% and good linearity (R2 > or = 0.9999) was obtained. A high degree of specificity, sensitivity as well as repeatability and reproducibility (RSD less than 2 and 5%, respectively) were also achieved. Chloroform was served as the most suitable solvent for extraction of 2,6-dimethoxy-1,4-benzoquinone. The optimised sample preparation and HPLC method can be practically used in the routine quality control process of F. foveolata stem extracts.

Two novel compounds from Ardisia punctata Lindl / 药学学报

To study the chemical constituents of Ardisia punctata,compounds were isolated with a combination of multi-chromatography.Their structures were determined on the basis of spectral analysis and comparison to those of the known compounds.A 1,4-benzoquinone derivative and a alkylphenol were isolated from the petroleum ether extract of the roots of Ardisia punctata.Their structures were elucidated as 2-tridecyl-3-[(2-tridecyl-4-acetoxy-6-methoxy)-phenoxyl]-6-methoxy-1,4-benzoquinone (1) and 2-methoxy-4-hydroxy-6-tridecyl-phenyl acetate (2).The two compounds are both new.

A new sesquiterpene lactone from the roots of Lasianthus acuminatissimus / 药学学报

Aim To study the active constituents for the treatment of rheumatoid arthritis from the ethyl acetate extracts of the roots of Lasianthus acuminatissimus Merr. Methods Various chromatographic techniques were used to separate and purify the constituents. Their structures were established on the basis of 1D, 2D NMR and HRMS spectroscopic analyses and their preliminary evaluation of anti-inflammation effect on the release of β-glucuronidase was carried out. Results Eight compounds were isolated and identified as lasianthuslactone A ( 1 ) , codonolactone ( 2 ), 2, 5-dimethoxy-1,4-benzoquinone ( 3 ) ,uncargenin A (4) , nonadecyl alcohol (5) , 13-docosenoic acid (6) , tetracosanoic acid (7) and β-sitosterol (8). Compound 3 showed a significant inhibitory effect on release of β-glucuronidase rat polymorphous nuclear leukocytes activated by platelet activating factor (PAF). Conclusion Compound 1is a new one, the others were isolated from the plant for the first time and 3 is one of active antiinflammation compound in the plant.

Three new belamcandaquinones from Ardisia punctata / 药学学报

Aim To study the chemical constituents of Ardisia punctata. Methods Compounds were separated with a combination of multi-chromatography. Their chemical structures were determined on the basis of spectral analysis and single crystal X-ray diffraction. Results Three compounds were isolated from chloroform extract of the roots of Ardisia punctata. Their structures were elucidated as 2-tridecyl-3-[ (2-tridecyl-3-acetoxy-4-methoxy-6-hydroxy) -phenyl ] -6-methoxy-1,4-benzoquinone ( 1 ), 2-tridecyl-3-[ ( 2 -tridecyl-4,6-dihydroxy ) -phenyl ] -6 -methoxy-1,4-benzoquinone ( 2 ) and 2 -tridecyl-3 - [ ( 2 -pentadecyl-4,6-dihydroxyl)-phenyl]-6-methoxy-1,4-benzoquinone (3). Conclusion The three compounds are new1,4-benzoquinone derivatives.